During an interview with Jeff Tweedy a few years ago, I asked the Wilco frontman whether he still preferred to listen to full albums, of if he’d joined the iPod generation and hit “shuffle.” Tweedy said that he did both, but added that he tended not to listen to his iPod when he was out and about. “I don’t like being in public with headphones on,” he said. “I don’t know how people can do it. It seems like you’re so cut off from your environment. I feel like I’d get hit by a car.”

I know what Tweedy means, both about feeling cut off and feeling faintly paranoid with headphones on. I like to take iPod-fueled walks on a nature trail near my house, and whenever I’m in the most isolated section of the woods—so far away from any buildings and roads that no one would hear me if I hollered for help—I wonder if I should turn off the music, so I can be alert to any serial killers or Satanists rustling around in the bushes. But I don’t hit pause, because the anxiety is part of the fun. Because what Tweedy may not realize is that the at-times-scary isolation of headphone-land is a feature, not a bug.

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Just as Coke tastes different depending on whether you drink it from bottle, can, or fountain, so does music sound different depending on the technology used to play it and the circumstances in which it’s heard. This isn’t just a matter of fidelity. Listening to an album through your laptop speakers at a reasonable volume while checking your email is different from cranking an album up loud while driving down a winding country road with the windows down. And listening through headphones changes the relationship with the music yet again. Headphones invite listeners to immerse, to hear sounds that that are barely audible through ordinary speakers. And, yes, it allows us to distance ourselves from the real world. When combined with actual interaction with the real world—taking a walk, for example—the disconnection adds another level of enjoyment. The music gets juxtaposed with whatever’s encountered along the way, serving as a soundtrack to the moment. And it’s all enhanced by the knowledge that at any moment, the reverie could be broken.

My first pair of headphones belonged to my father. They were the old-fashioned kind, large and cushioned, with a long, curly, easily tangled cord, and individual volume knobs on each ear. My older brother commandeered them when we were kids, and would listen to the Star Wars soundtrack at high volume, cranking all available knobs to the max for the final triumphant notes. They later became his headphones, then mine when he went off to college. They were bulky and crackled when I adjusted the ear volume, but my God, did they ever block out sound. I spent much of my adolescence in my bedroom, reading and writing and listening to music, perpetually jumpy because my mother would knock on the door and walk in without my ever having heard her.

Then came the Walkman era, and the advent of cheap headphones with thin foam padding and fragile plastic adjusters—the kind of headphones that needed to be replaced roughly every three months. I rarely had any money to speak of, so I bought the most bargain-basement equipment I could find, which meant the headphones broke even faster. The cushions would shred, the adjusters would snap—causing an entire speaker to fall off spontaneously, mid-song and mid-stride—and the wires would get caught on doorknobs and chair backs, ripping the whole contraption off violently.

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To avoid ponying up 10 bucks, I got creative with masking tape. And when the sound started to flicker, I learned how to turn the plug or bend the wires until I had sound in both ears again. Annoying? Sure. But the hoops we have to jump through to keep our technology working can be endearing, too. The clever jerry-rig, or the temporary patch that holds for months… these bind us to our gadgets. I could never hand my Walkman and headphones over to others without giving them a list of instructions for how to make the unit work, all the while knowing that no one was ever going to be able to coax the sound out properly the way I could. I played that cassette deck like a concertina.

Though I’ve been able to afford good headphones for a while now, I still can’t go top-of-the-line. Even good headphones break. They get sat on, or hung on something, or jostled and crushed in a carry-on bag. So I buy the not-quite-bottom-shelf merchandise, and buy in bulk. (Because as much as I may romanticize the days of jiggling wires, these days I’d rather replace the bum gear than stop every few minutes to fiddle with a jack.)

I’ve also switched to earbuds, which I used to hate, because they provoked earaches and never seemed to stay in all that well. With the native iPod earbuds, I find myself constantly pressing at them, never sure that they’re all the way in. (It’s like when I go to a 3D movie; I can never get the glasses to fit right over my specs, so I spend the entire movie fidgeting.) But last year I found a good $20 pair of noise-canceling earbuds with cushioned, protruding speakers that fit tightly and comfortably in the ear. They remind me of those big bulky headphones that I had as a teenager, in that when I’m using them, I can’t really hear anything outside of the sound coming through. I bought them because I wanted to listen to music (and baseball) in bed without disturbing my wife with audio-bleed. But they make me a little anxious, because while I have them in, I can’t hear what’s going on in the house. Did one of the kids just wake up? Did the furnace make a weird noise? Is there a prowler? The uncertainty adds some urgency.

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That urgency’s magnified when I use them outside. Anyone who’s ever walked around with a portable music-player knows the awkwardness of passing by a friend, a neighbor, or even a stranger who yells out a hello and then follows it up with a question, obligating you to fish the player out of your pocket, press pause, and take off your headphones. (Usually the question is, “Out for a walk?”) If you want to make a point, you can go through the music-pausing ritual very slowly, to illustrate the inconvenience. I confess I’ve done this myself on my bad days. More often though, having the headphones on or the earbuds in cues everyone that you’re in your own world, such that you can get by with a smile and wave.

And once you’re in that world, you’re free in a way you rarely are when listening on a home stereo or in a car. Turn the music up loud. It’s okay. Listen to profanity-laced hip-hop, or giddy showtunes, or The Best Of Poco. No one will judge you. If you get hit by a car, at least you’ll die on your own terms, with a song to play you out.